April 3, 1986. Hard to believe, but it was 27 years ago today that The Cosby Show episode "Theo's Holiday" (season 2, episode 21) aired and the show firmly cemented itself as the greatest family comedy of the '80s. In my opinion, it was the best episode in the series run. In the classic ep, Theo Huxtable finds himself taking his parents' money for granted, so they decide to teach him a lesson about the real world—and the writing team of Carsey-Werner-Mandabach could not have illustrated it any more brilliantly. Theo: “When I get in the real world, I'm going to have a lot of money!” Cliff: “I hope you're not waiting for me to die.” Theo spends the night at Cockroach's, and when he arrives home the next morning, nothing is as it seems. There's Vanessa, as Margo Farnsworth, Theo's potential new neighbor—and Cliff as Harley Weewax, Theo's potential new landlord. And then there's me, wanting to know how on earth the writers came up with these names. ...while Phylicia Rashad makes her debut as Millie Farquar, who runs the Chuck Wagon Restaurant. And Theo's face does this: Theo: "Good one, Mom!" Millie: "Whoooo?" Then there's Mrs. Griswald, played read more